WO2007069733A1 - Procede de fabrication d’une substance apparentee au ceramide utilisant une solution alcaline aqueuse et appareil pour la fabrication - Google Patents

Procede de fabrication d’une substance apparentee au ceramide utilisant une solution alcaline aqueuse et appareil pour la fabrication Download PDF

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Publication number
WO2007069733A1
WO2007069733A1 PCT/JP2006/325075 JP2006325075W WO2007069733A1 WO 2007069733 A1 WO2007069733 A1 WO 2007069733A1 JP 2006325075 W JP2006325075 W JP 2006325075W WO 2007069733 A1 WO2007069733 A1 WO 2007069733A1
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Prior art keywords
ceramide
related substance
extraction
extract
aqueous solution
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PCT/JP2006/325075
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English (en)
Japanese (ja)
Inventor
Takahiro Ishikawa
Reina Touyama
Kouji Takeuchi
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Dna Bank Co., Ltd.
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Priority to JP2007550246A priority Critical patent/JPWO2007069733A1/ja
Publication of WO2007069733A1 publication Critical patent/WO2007069733A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B11/00—Recovery or refining of other fatty substances, e.g. lanolin or waxes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical

Definitions

  • the present invention relates to a method and apparatus for producing a ceramide-related substance for biological tissue strength using an alkaline aqueous solution.
  • Ceramide is a kind of lipid and is a substance having a structure in which sphingosine and a fatty acid form an acid amide bond.
  • the “ceramide-related substance” refers to a sphingolipid having the ceramide as a basic skeleton. Ceramide-related substances are bisected into sphingoglycolipids with sugars bound to ceramides and sphingophospholipids with phosphates and bases bounded, and a number of molecular species are known for these two sphingolipids.
  • ceramides and ceramide-related substances are present on the cell membranes of various organisms, and function in the skin as a moisturizing ingredient that prevents the evaporation of water from stratum corneum, as well as cell differentiation and proliferation, apoptosis induction, and information. It has become clear that it fulfills various physiological functions in transmission, nerve function, etc.
  • Ceramide-related substances are relatively widespread in the tissues of animals and plants, especially in the brain and nerve tissues of animals. For this reason, ceramide-related substances that have been extracted from the brain power of cattle and other livestock have been mainly used.
  • BSE bovine spongiform encephalopathy
  • the safety of ceramide-related substances obtained from livestock brain has become a problem.
  • a new raw material or substitute for a ceramic-related substance that is safe for the human body instead of the brain of livestock has been demanded.
  • Patent Document 1 is an invention for a therapeutic agent for atopic dermatitis comprising sunggo glycolipid extracted from an organic solvent as an active ingredient.
  • plant cells mainly contain glyce oral glycolipids, and there are few ceramide-related substances such as glycosphingolipids compared to animal cells. In order to obtain a sufficient amount of ceramide-related substances, a large amount of raw materials is required, which raises the problem of high manufacturing costs.
  • Patent Document 2 There is an invention of Patent Document 2 as one method of reducing production costs while using plants as raw materials.
  • This invention is a method for producing barley malt oil containing a ceramide-related substance from beer lees. Beer lees contain a relatively large amount of ceramide-related substances and are a by-product generated during the beer production process, so they are superior in terms of cost reduction compared to conventional plant materials. However, since beer lees contain a large amount of water, the polar solvent for extraction is diluted immediately. Therefore, in order to extract sufficient ceramide-related substances from beer lees, a large amount of polar solvent exceeding the dilution must be used. This hinders further reduction in manufacturing costs.
  • Patent Document 3 is a method for further solving the problem of Patent Document 2.
  • Patent Document 3 provides a method for sufficiently drying beer lees to extract ceramide-related substances efficiently and at low cost, and a method for repeating a cycle in which the obtained extract is used again as a polar solvent for extraction. is doing.
  • the amount of polar solvent required for extraction can be reduced to about 1Z10 of the conventional method.
  • there arises a problem of an increase in cost accompanying an increase in the number of processes such as a drying process and a cycle process.
  • Patent Document 1 JP 2003-231640
  • Patent Document 2 JP-A-11 193238
  • Patent Document 3 # 112005-272639
  • An object of the present invention is to provide a method and an apparatus for producing a ceramide-related substance from a living tissue without using an organic solvent such as ethanol in an extraction process in order to reduce production costs.
  • Another object of the present invention is to provide a method and apparatus for reducing the number of manufacturing processes while maintaining the same extraction accuracy as that of the conventional method.
  • the present inventors go through an extraction process using an organic solvent by directly immersing a living tissue in an alkaline aqueous solution and dissolving the cells themselves constituting the living tissue.
  • the present invention has been completed based on such a method, and provides a method for producing a ceramide-related substance shown in (1) to (7) below and a production apparatus for producing it as shown in (8).
  • the present invention provides an extraction step of extracting a ceramide-related substance by immersing a biological tissue prepared without an organic solvent extraction step in an alkaline aqueous solution, and an extract obtained in the extraction step.
  • a method for producing a ceramide-related substance comprising a separation step for separating insoluble substances and a concentration step for concentrating the extract separated in the separation step is provided.
  • the present invention provides a method for producing a ceramide-related substance, wherein the extraction step is performed by heating, Z, or pressurizing a biological tissue immersed in an alkaline aqueous solution.
  • the present invention provides a method for producing a ceramide-related substance, wherein the alkaline aqueous solution strength in the extraction step is in the range of from H11 to pH14.
  • the present invention provides a method for producing a ceramide-related substance, wherein the heating in the extraction step is in a range of 105 ° C or higher and 130 ° C or lower.
  • the present invention provides a method for producing a ceramide-related substance, wherein the pressure in the extraction step is in the range of 1.2 atm or more and 2.2 atm or less.
  • the present invention provides a method for producing a ceramide-related substance, wherein the living tissue is a plant-derived tissue.
  • the present invention provides a method for producing a ceramide-related substance, which is a beer koji obtained in the process of producing the above-described plant-derived tissue-powered beer and the like.
  • the present invention provides an extraction unit for extracting a ceramide-related substance by immersing a biological tissue prepared without passing through an organic solvent extraction unit in an alkaline aqueous solution, and an extract obtained by the extraction unit insoluble
  • a ceramide-related substance manufacturing apparatus comprising a separation unit for separating a product and a concentration unit for concentrating the extract separated by the separation unit.
  • a target ceramide-related substance can be extracted without using any organic solvent such as ethanol in the extraction process.
  • organic solvent such as ethanol
  • the alkaline salt used is, for example, much cheaper than ethanol when potassium carbonate is used. Therefore, a significant reduction in manufacturing cost can be expected.
  • the method for producing a ceramide-related substance of the present invention it is possible to reduce the production process while maintaining the same extraction accuracy as that of the conventional method.
  • the raw material can be used in the extraction process as it is without being subjected to processing such as a pulverization process and a drying process.
  • the alkali hydrolysis step for saponification of glyce oral glycolipid which has been conventionally performed after the extraction step in order to increase the purity of the quality, can be performed simultaneously in one step of the extraction step.
  • the method for producing a ceramide-related substance of the present invention it is possible to produce a ceramide-related substance that is equal to or better than a ceramide-related substance obtained by a conventional production method in terms of safety in use of the produced ceramide-related substance to the human body.
  • a ceramide-related substance obtained by a conventional production method in terms of safety in use of the produced ceramide-related substance to the human body.
  • potassium carbonate is used as an alkali salt in preparing an alkaline aqueous solution
  • potassium carbonate is the main component of “Kansui”, which is approved for use as a food additive. If so, the impact on the human body is said to be extremely small.
  • the solvent used for extraction is an alkaline aqueous solution
  • the existing equipment can be diverted.
  • equipment such as a boiling process kettle and a filtration process filtration device used for beer production in a beer manufacturing plant are used in the extraction process kettle and separation process filtration of the present invention. Each can be diverted to a device.
  • Embodiment 1 describes claims 1 to 7 and the like.
  • the second embodiment will explain claim 8 and the like.
  • Embodiment 1 relates to a method for producing a ceramide-related substance.
  • the production method of the present embodiment extracts a ceramide-related substance by directly immersing a biological tissue including a plant-derived tissue such as beer lees in an alkaline aqueous solution without going through an organic solvent extraction step. It is characterized by saponifying a glyce oral glycolipid extracted in an alkaline aqueous solution.
  • FIG. 1 shows each process and its flow in the first embodiment.
  • the present embodiment is composed of process powers of an extraction process (S0101), a separation process (S0102), and a concentration process (S0103).
  • S0101 extraction process
  • S0102 separation process
  • S0103 concentration process
  • the "extraction step” is a step of extracting a ceramide-related substance by immersing a biological tissue prepared without going through an organic solvent extraction step in an aqueous alkaline solution. This extraction step is performed prior to the separation step (S0102) and the concentration step (S0103).
  • Bio tissue is a raw material in the present invention, and is all or a part of a body constituting an organism.
  • the organism may be a single cell organism such as yeast, or a multicellular organism such as an animal or plant.
  • multicellular organisms there are no particular restrictions on the organ or tissue site used.
  • animals it is preferable to use brains, nerve organs and the like that contain a large amount of the target ceramide-related substance for production efficiency.
  • plant-derived tissue it is preferable to use plant-derived tissue until the problem is solved.
  • beer lees obtained in the manufacturing process of beer are particularly preferred. This is because, as described in Example 2, according to the present invention, the target ceramide-related substance can be most efficiently produced from beer lees.
  • Beer or the like means beer or beer-like liquor.
  • “beer-like liquor” refers to an alcoholic beverage having an appearance and flavor similar to beer. For example, Happoshu.
  • the first step in the general beer production process is the malt production process (0301).
  • the malt production process (0301).
  • dry malt is obtained by drying with hot air or the like to stop the growth.
  • preparation process (0302).
  • the dried malt is pulverized, and warm water and auxiliary materials are added, and the starch is processed by the action of the malt enzyme.
  • the wort is filtered.
  • Residue (030 7) is a beer lees called malt feed.
  • a boiling step (0303) is performed.
  • the wort is boiled and hops, which are bitter components, are added. Protein and hop koji (0308) produced by boiling are precipitated and removed.
  • the fermentation process (0304). In this step, the boiled wort is cooled, and yeast is added and fermented for about 1 to 2 weeks (depending on the fermentation temperature). Subsequently, the aging process (0305) is entered. In this process, the wort after the fermentation process is cooled to near 0 ° C to suppress fermentation. Here, the carbon dioxide gas accumulates and the taste becomes mellow. The last is the filtration step (0306). In this step, the beer is also obtained by filtering the yeast (0309) after the aging step. After filtration, the heat-sterilized beer is normal beer.
  • Beer lees is a residue obtained after the charging process in the manufacturing process of the beer and the like.
  • malt in addition to malt, it is also composed of rice, corn starch, potato and other starches that are used as auxiliary ingredients, sugar-containing grains, and squeezing power such as potatoes. Of course, it may be a residue composed of 100% malt mash.
  • protein or hop koji (0308) obtained after the boiling step (0303) or yeast (0309) obtained after the filtration step (0306) may be obtained as a part of the beer koji. Hops and yeasts have the potential to be mixed with squeezed juice or ceramide-related substances to be extracted that have moved to the fermentation process.
  • the "organic solvent extraction step” is an extraction step that uses an organic solvent such as ethanol when extracting lipid components from living tissue, and is naturally essential for conventional methods for producing ceramide-related substances. It was considered a process.
  • the present invention does not require this step. That is, the present invention is characterized in that a biological tissue prepared without going through an organic solvent extraction step can be used as it is in the extraction step of the present invention! /
  • Alkaline aqueous solution is an aqueous solution having alkali properties and is an extraction solvent used in the extraction step.
  • the aqueous solution does not contain an organic solvent such as ethanol.
  • the aqueous solution is prepared by dissolving an alkali salt in water.
  • the alkali salt to be used is not particularly limited. For example, sodium hydroxide (NaOH), potassium hydroxide (KOH), sodium carbonate (Na CO), or potassium carbonate (K CO) can be used.
  • carbonate such as potassium carbonate or sodium carbonate Salt is the main component of “Kansui” approved as a food additive and has a very small influence on the human body, and is therefore preferred as the alkali salt used in this embodiment.
  • the alkaline aqueous solution functions for cell lysis and saponification (alkali hydrolysis) of glyceglycoglycolipid eluted in the aqueous solution by the lysis. Accordingly, the pH of the alkaline aqueous solution used in the present embodiment needs to be sufficient to lyse cells. Specifically, it is preferable that the pH of the alkaline aqueous solution immediately before use is in the range of pH 11 to pH 14.
  • a step of previously drying or crushing the biological tissue as a raw material is not necessarily required. This is because even if the raw material contains a large amount of water, the pH of the alkaline aqueous solution is hardly affected when immersed in an alkaline aqueous solution having a volume described later. In fact, as shown in Example 4, even if beer lees having a water content of about 60% are used as raw materials, the target ceramide-related substance can be produced according to this embodiment.
  • a biological tissue drying process or grinding process may be added prior to the extraction process.
  • drying method in the drying step and the pulverization method in the pulverization step may be performed according to known techniques.
  • the amount of the alkaline aqueous solution is within the range of 5 to 15 times the volume of the alkaline aqueous solution to the weight of the biological tissue, that is, the volume Z weight (VZW). It is preferable to do. More preferably, it is in the range of 8 times to 12 times. Within these ranges, as described above, even if the raw material contains a large amount of water, the raw material itself is strong and acidic, and unless otherwise, the pH of the aqueous solution is hardly affected. is there. Furthermore, it is also sufficient to saponify glyceglycoglycolipid dissolved in the aqueous solution. To explain with a specific example, an alkaline aqueous solution may be used in a range of 25 ml to 75 ml for 5 g of living tissue.
  • extracting refers to releasing a ceramide-related substance contained in a living tissue into an aqueous alkali solution.
  • the conventional extraction process using organic solvents elutes only fat components into organic solvents while maintaining the structure of living tissue. It was.
  • the protein constituting the living tissue is denatured with alkali. Thereby, the biological tissue, and further the cell wall and the cell membrane itself are dissolved, and the ceramide-related substance that has been contained in the cell or fixed to the cell membrane until then is released into the alkaline aqueous solution.
  • the extraction step of the present embodiment is also a step of lysing cells with alkali to release the aforementioned ceramide-related substance into an aqueous alkali solution and saponifying the glyceglycoglycolipid released into the aqueous solution.
  • this is similar to the alkaline water splitting process associated with the conventional organic solvent extraction process.
  • the conventional alkali hydrolysis step is configured to saponify glyceglycoglycolipid in the lipid component extracted in an organic solvent
  • the method of this embodiment does not provide lipid from biological tissue. The purpose is to release the components and to saponify the glycated glycolipid.
  • the configuration requirements for both are also different.
  • the alkali hydrolysis step of the conventional method was sufficient if it was heated to about 50 ° C. to 60 ° C.
  • 95 ° C. or higher described later is obtained. Preferred to heat to.
  • the alkali hydrolysis step associated with the organic solvent extraction step of the conventional method and the extraction step of the present embodiment are steps in which the configurations are different.
  • the glycated oral glycolipid is decomposed into fatty acid and glycerin by the saponification.
  • the biological tissue strength is also extracted through the two steps of extracting the lipid component with an organic solvent such as ethanol and then saponifying the glyceglycoglycolipid contained in the obtained lipid component.
  • an organic solvent such as ethanol
  • saponifying the glyceglycoglycolipid contained in the obtained lipid component There was a need.
  • plant tissues contain a large amount of glycoglycoglycolipids as glycolipids, and there is only a very small amount of sphingoglycolipid, a ceramide-related substance.
  • the alkaline hydrolysis step is an important step in removing unnecessary glyce-mouth glycolipids.
  • the extraction step can be saponified at the same time as the extraction, the same effect as the conventional technique can be obtained with only one step. Also in this respect, the method of the present embodiment is very useful.
  • the experimental results of saponification by the extraction process are shown in Example 4.
  • the heating temperature may be 95 ° C or higher and 140 ° C or lower. If it is lower than 95 ° C, it is insufficient for extraction of ceramide-related substances, and if it exceeds 140 ° C, the target ceramide-related substances may be denatured.
  • the desired temperature for extraction efficiency is in the range of 105 ° C to 130 ° C.
  • concentration of alkaline aqueous solution which is an extraction solvent you may stir the said solvent with a heating.
  • the stirring method corresponds to, for example, stirring using a stirring bowl stirring device.
  • the heating method is not particularly limited as long as the temperature of the living tissue can be raised to the above temperature range.
  • it may be heated by a heat source such as a heater or microwave in a tank equipped with a temperature control device! You can also heat it in a container and adjust the heating power by direct fire.
  • the pressure to be applied may be 1 atm or more and 2.5 atm or less. This is to achieve the above-mentioned heating temperature of 95 ° C or more and 140 ° C or less.
  • the desired temperature for extraction efficiency is in the range of 105 ° C to 130 ° C.
  • the desired pressure to achieve this temperature is in the range of 1.2 to 2.2 atm.
  • the method of pressurization is not particularly limited as long as the above-described pressure can be achieved.
  • an autoclave device or a household pressure cooker may be used.
  • the “separation step” (S0102) is a step performed subsequent to the extraction step, and is a step of separating the extract obtained from the extraction step and the insoluble matter.
  • the alkaline aqueous solution obtained after the extraction step is in a mixed state in which the later-described extract and insoluble matter are mixed, and this separation step is a step for obtaining the extract from the mixed solution.
  • the “extract” is a liquid component of biological tissue dissolved in an aqueous solution by the action of an alkaline aqueous solution and an alkali.
  • a fine solid component that remains after the insoluble matter described later is separated and can be easily recognized, and it may be mixed in the extract solution, even if it is not a liquid component, as long as it is of a particle level.
  • the extract is a ceramide solution eluted from living tissue.
  • lipid components such as continuous substances, it contains various components such as fatty acids and glycerin produced by saponification of denatured protein glyce oral glycolipids.
  • the “insoluble matter” is a solid component that remains without being dissolved in the alkaline aqueous solution in the extraction step.
  • the insoluble matter is not necessarily insoluble in the alkaline aqueous solution, but also contains components that are dissolved in the alkaline aqueous solution through the extraction process again as described in the re-immersion of the insoluble matter described later.
  • the separation method is not particularly limited as long as it can separate the extract from the insoluble matter.
  • it may be any of filtration, centrifugation, stationary precipitation, or a combination thereof.
  • Filter materials used for filtration include, for example, paper filters, membrane filters, fabric filters, Tyacol filters, hollow branch membrane filters, mouth filter, celite, diatomaceous earth filters, and combinations thereof.
  • the structure of the filter used for filtration may be a single layer or multiple layers. In the case of a multilayer filter, it may be composed of the same type of layer or a plurality of different types of layers. Furthermore, in the case of a multilayer filter, as long as it is configured to be able to pass through each layer, it is not always necessary that the layers are directly stacked, and the layers may be separated. For example, connect a plurality of columns packed with each filter via piping so that they can be filtered.
  • the separation method of the extract and insoluble matter is not limited.
  • the alkaline aqueous solution after the extraction step may be introduced into a porous tube and centrifuged in a centrifuge to collect only the extract that also releases pores, or may be introduced into a non-porous tube and then into the centrifuge. After centrifugation, only the extract that is the supernatant may be collected. Further, the gravity acceleration (G) of centrifugation may be appropriately determined in consideration of the permissible level of insoluble matter mixed in the extract of the present invention.
  • the “concentration step” (S0103) is a step that is performed after the separation step and is a step of concentrating the extract separated in the separation step.
  • concentration means the following two Can be broadly divided.
  • the first “concentration” is to remove all or part of the water from the alkaline aqueous solution of the extract, and to increase the concentration of the ceramide-related substance in the liquid if the final product is a liquid.
  • any method known in the art may be used as long as it is a method capable of removing water from the extract solution without denaturing the ceramide-related substance.
  • an evaporation concentration method using an evaporator or an air-dry evaporation concentration method in which moisture is evaporated by blowing air can be used.
  • the final product obtained is in a state containing impurities, in other words, a mixture of denatured protein, dariserine, fatty acid, precipitated alkali salt and the like in addition to the target ceramide-related substance.
  • the product obtained after the concentration step may be in a state where impurities are mixed.
  • the subsequent steps may be appropriately added according to the purpose and necessity of the subsequent use of the ceramide-related substance, and are not necessarily required for producing the ceramide-related substance.
  • the mixture of denatured protein, glycerin and fatty acid is not particularly problematic.
  • the removal of the alkali salt is, for example, insoluble in ethanol if the alkali salt used is potassium carbonate, so the final product is mixed with an appropriate amount of ethanol to remove the solid components (potassium carbonate precipitated). Can be achieved. If the purity of the ceramide-related substance needs to be further increased, it may be concentrated by the method described in “(2) Crude purification of ceramide-related substance by extraction solution” described later. As described above, even if impurities are mixed in the product obtained after the concentration step, the effect of this embodiment is not reduced at all.
  • the second “concentration” is to separate and remove impurities other than the ceramide-related substance contained in the extract, and to roughly purify the ceramide-related substance.
  • the rough purification method is not particularly limited as long as it is an appropriate purification method.
  • known Technical cooling and purification methods can be used.
  • the "cooling purification method” is a method that utilizes the property that lipid components including ceramide-related substances precipitate at a low temperature. For example, when the extract is cooled to 4 ° C, lipid components such as ceramide-related substances dissolved in the extract are deposited. This can be accomplished by standing or cooling and collecting as a sediment, or filtering and collecting as a residue.
  • the method for producing a ceramide-related substance it is possible to obtain a target ceramide-related substance without using an organic solvent throughout the entire process as well as the extraction step.
  • the use of organic solvents is inevitable for purification.
  • the following organic solvent separation method may be used.
  • this method is a method that can be appropriately performed according to the purpose and necessity of the use of the ceramide-related substance, which is not an essential constituent element for the concentration step.
  • fatty acid and glycerin which are degradation products of glyce-mouth glycolipids transferred to the aqueous layer, and denatured proteins transferred to the intermediate layer are removed.
  • Recovered black mouth form strength By removing the black mouth form by air drying or the like, a highly purified ceramide-related substance can be obtained.
  • the roughly purified ceramide-related substance may be further purified as necessary.
  • a ceramide-related substance when used as a pharmaceutical composition, its purity needs to be higher.
  • the obtained ceramide-related substance can be purified by further fractionation.
  • the fractionation method may be in accordance with known techniques. For example, a method of fractionating and eluting by thin layer chromatography (TLC), adsorption chromatography, partition chromatography, high performance liquid chromatography (HPLC) and the like is applicable. Specific examples of chromatography include column chromatography.
  • the column chromatography is After the crude purified product of ceramide-related substance was loaded on a stationary phase such as silica gel, a hydrophobic solvent such as black mouth form, a hydrophilic solvent such as methanol, and a plurality of these solvents were mixed in an appropriate volume ratio. Elute with eluate. During elution, adjust the eluate composition, elution time, etc. as appropriate.
  • the target ceramide-related substance can be separated and purified almost purely by repeating the same operation several times as necessary, depending on the difference in solubility and ionic bond strength of the ceramide-related substance in the solvent.
  • the above-mentioned concentration may be a deviation! /.
  • the above enrichment may be combined. Specifically, prior to the method of cooling and purifying ceramide-related substances from the extract, the extract solution is removed to a certain extent to obtain a high concentration state.
  • the insoluble matter separated in the separation step often contains ceramide-related substances that cannot be completely extracted by the previous alkaline aqueous solution. Therefore, in order to improve the recovery efficiency of the ceramide-related substance from the living tissue and weave, the remaining ceramide-related substance may be extracted by re-immersing the insoluble material in a new alkaline aqueous solution.
  • the method for producing a ceramide-related substance according to the present embodiment includes a second extraction step of extracting the ceramide-related substance by immersing the insoluble matter separated in the separation step again in an alkaline aqueous solution, and the second extraction step. It further has the 2nd separation process which isolate
  • FIG. 2 shows a process and flow in the case of re-immersing insoluble matter.
  • this embodiment also includes the process power of the extraction process (S0201), the separation process (S0202), the second extraction process (S0203), the second separation process (S0204), and the concentration process (S0205).
  • S0201 the extraction process
  • S0202 the separation process
  • S0203 the second extraction process
  • S0204 the second separation process
  • concentration process S0205
  • the “second extraction step” is a step of extracting the ceramide-related substances by immersing the insoluble matter separated in the separation step again in an alkaline aqueous solution.
  • the basic structure of the second extraction step is the same as that of the extraction step except that the insoluble material is used as a raw material and the substrate is immersed in a new alkaline aqueous solution.
  • the insoluble matter can be used as it is after the separation step, and no special confirmation is required before the second extraction step. Of course, through the drying process, etc. It doesn't matter.
  • the “second separation step” (S0204) is performed subsequent to the second extraction step, and is a step of separating the second extract from the second insoluble matter.
  • the second extract is an extract obtained in the second extraction step, and is considered to contain a ceramide-related substance that cannot be extracted in the previous extract.
  • the second insoluble matter is a solid component that remains without being dissolved in the alkaline water solution even in the second extraction step.
  • the basic configuration of the second separation step is the same as that of the extraction step.
  • the second extract obtained after the second separation step may be mixed with the previously obtained extract as shown in Fig. 2 to carry out a concentration step.
  • the concentration step may be performed independently of the extracted liquid.
  • the configuration of the concentration step is the same as described above.
  • the ceramide-related substance obtained in the present embodiment can be used in pharmaceutical compositions, skin moisturizers, health foods and the like.
  • the "pharmaceutical composition” as used herein refers to an antitumor agent, an immunostimulant, an apoptosis inducer, a neuronal cell activator, or the like that is widely used as a pharmaceutical or a raw material thereof.
  • the pharmaceutical composition comprising the ceramide-related substance obtained in the present embodiment as an active ingredient is administered to humans or animals by making the ceramide-related substance as it is or a pharmaceutical preparation formulated with an appropriate carrier. can do.
  • the administration method as a pharmaceutical preparation is not particularly limited as long as it is a suitable administration route.
  • intravascular administration to veins or arteries intraperitoneal administration, intrathoracic administration, intramuscular administration, rectal administration, subcutaneous administration, percutaneous absorption, oral administration, or It can be administered by methods such as sublingual administration.
  • administration can be carried out by methods such as local administration by injection or the like, intravascular administration to veins or arteries, intraperitoneal administration, and subcutaneous injection.
  • the dosage form of the pharmaceutical preparation may be appropriately selected according to the administration method, purpose of administration and the like! example For example, tablets, capsules, fine granules, powders, mouth preparations, dry syrups, etc. for oral preparations, and injections, suspensions, emulsifiers, ointments, suppositories, coatings, etc. for parenteral preparations Can be mentioned.
  • the carrier used for formulation into a pharmaceutical preparation may be appropriately selected from pharmaceutically acceptable additives depending on the administration method, administration purpose and the like.
  • additives include diluents such as solvents and soluble additives, pH adjusters, thickeners, tonicity agents, excipients, binders, lubricants, stabilizers, preservatives. , Antioxidants, surfactants and the like.
  • the dose of the ceramide-related substance may be determined so as not to exceed a certain amount when administered continuously or intermittently in consideration of the results of animal experiments and individual circumstances.
  • the specific dose varies depending on the administration method and the patient's situation.
  • “situation” includes, for example, age, sex, body weight, diet, administration time, concomitant drug, drug sensitivity, and degree of disease. Appropriate dose, dose and number of doses should be determined by expert dose determination tests based on the above guidelines.
  • Skin moisturizer has the effect of preventing the evaporation of moisture contained in the skin stratum corneum and maintaining the moisture of the skin, and also has the effect of giving the product a water retention effect when blended into the product.
  • polyhydric alcohols such as glycerin, fats and oils such as coconut oil and olive oil, and ceramide and ceramide-related substances are applicable.
  • the method of use as a skin moisturizer is not particularly limited as long as it is a transdermal absorption method.
  • the dosage form of the skin moisturizing agent may be appropriately selected depending on the administration method, administration purpose, and the like! Examples include suspending agents, emulsifiers, ointments, coating agents and the like. Specifically, it can be used in cosmetics such as hand creams and lipsticks, hair straighteners, rinses, ointments, etc. that are applied directly to the skin or hair for the purpose of evaporating moisture from the stratum corneum. It is good to add or weave it into clothing fibers that come in direct contact with the skin, such as underwear or socks.
  • Health food refers to all foods that are sold * used as foods that normally contribute to maintaining and improving health.
  • the health food in this embodiment is not limited to the above meaning. It means all foods mixed with ceramide-related substances obtained in the embodiment.
  • the intake method as a health food is not particularly limited as long as it is an oral method. What is necessary is just to select suitably according to the objective.
  • the ceramide-related substance can be provided so that it can be ingested by humans or animals as it is or after being processed with an appropriate carrier. For example, it can be filled in capsules as it is, or it can be processed into tablets, capsules, fine granules, powders, mouthpieces, dry syrups, etc. by adding carriers.
  • an additive acceptable as a food may be appropriately selected depending on the administration method, administration purpose, and the like.
  • additives include diluents such as solvents and solubilizers, pH adjusters, thickeners, tonicity agents, excipients, binders, lubricants, stabilizers, preservatives, antioxidants This applies to drugs.
  • the excipient is dextrin, starch, lactose, or the like, but is not limited thereto as long as the same effect can be obtained.
  • the excipient content is preferably in the range of 40% to 90%.
  • ceramide-related substances may be used in addition to raw materials as processed food materials or additives.
  • a target ceramide-related substance can be extracted without using any organic solvent such as ethanol in the extraction step.
  • the ceramide-related substance manufacturing method of the present embodiment it is possible to significantly reduce the manufacturing process while maintaining the same extraction accuracy as that of the conventional method.
  • a ceramide-related substance to be produced can be produced at a level equivalent to or higher than that of a ceramide-related substance obtained by a conventional production method in terms of safety in use for the human body.
  • Embodiment 2 relates to a ceramide-related substance manufacturing apparatus based on the ceramide-related substance manufacturing method of Embodiment 1. According to this embodiment, it is possible to industrialize ceramic-related substances by the method of Embodiment 1.
  • Embodiment 2 Configuration>
  • FIG. 4 shows the configuration of the second embodiment.
  • the quality production apparatus (0400) is composed of an extraction unit (0401), a separation unit (0402), and a concentration unit (0403).
  • each component will be described.
  • the "extraction section” (0401) is configured to extract a ceramide-related substance by immersing a biological tissue prepared without going through an organic solvent extraction section in an alkaline aqueous solution.
  • the specific configuration and procedure in the main extraction unit follow the extraction step (S0101) of the first embodiment.
  • the "separation unit” (0402) is configured to separate the extract obtained from the extraction unit from the insoluble matter.
  • the specific configuration and procedure in the separation unit are in accordance with the separation step (S0102) of the first embodiment.
  • the "concentration section” (0403) is configured to concentrate the extract separated in the separation section.
  • the specific configuration and procedure in the concentrating unit follow the concentrating step (S0103) of the first embodiment.
  • FIG. 5 shows another configuration of the second embodiment.
  • the ceramide-related substance production apparatus (05 00) shown in this figure also comprises the extraction section (0501), separation section (0502), second extraction section (0503), second separation section (0504), and concentration section (0505) force. May be.
  • the second extraction unit (0503) and the second separation unit (0504) will be described.
  • the "second extraction unit” (0503) is configured to extract the ceramide-related substance by immersing the insoluble matter separated in the separation unit again in an alkaline aqueous solution.
  • the specific configuration and procedure in the second extraction unit follow the second extraction step (S0203) of the first embodiment.
  • the "second separation unit” (0504) is configured to separate the second extract obtained from the second extraction unit from the insoluble matter.
  • the specific configuration and procedure in the second separation unit follow the second separation step (S0204) of the first embodiment.
  • the concentration unit in Fig. 5 is configured so that both the extract and the second extract can be concentrated.
  • a plurality of concentration units exist in one ceramide-related substance production apparatus, and the extract and The second extract and the second extract may be configured to be independently concentrated.
  • the ceramide-related substance production apparatus of the present embodiment does not require an organic solvent such as ethanol in principle because an alkaline aqueous solution is used as the extraction solvent. Therefore, each part and the piping that connects each part are treated with an organic solvent-resistant, corrosion-resistant treatment or material. No need to use. Therefore, the ceramide-related substance manufacturing apparatus of the present embodiment can be used for existing equipment without requiring a large capital investment for the equipment. For example, when using beer lees as a raw material, the ceramide-related substance manufacturing apparatus of this embodiment may use an existing beer manufacturing facility. Specifically, the boiling pot used in the boiling step (0303) in the beer production process shown in FIG. 3 can be used as the extraction unit (0401, 0501) of this embodiment.
  • the filtration tank used in the filtration step (0306) in the beer production step can be used as the separation unit (0402, 0502) of the present embodiment.
  • Embodiment 2 Process Flow>
  • the process flow of the present embodiment is in accordance with the process flow of the first embodiment shown in FIGS.
  • each unit may be configured to be controllable by a computer.
  • Computers mentioned here include hardware components such as CPU, memory, bus, hard disk drive, media reading drive such as CD-ROM and DVD-ROM, transmission / reception ports for various communications, interfaces, and other peripheral devices, Driver programs and other application programs for controlling these hardware are also configured.
  • Examples of programs for causing a computer to execute control of each unit include the following. First, in the extraction process, the amount of raw material taken into the extraction unit and the appropriate volume and pH of the alkaline aqueous solution are controlled, and the temperature and pressure in the extraction unit are further extracted during heating and pressurization.
  • the concentration process is a program that allows a computer to select a concentration method and manage temperature and time for concentration.
  • Such a program that causes a computer to execute the manufacturing apparatus of the present embodiment can also constitute a part of the present invention as software.
  • other software products used to cause computers to execute such software and the same products
  • a recording medium in which is fixed to the recording medium is also included in the technical scope of the present invention.
  • this device By sequentially executing the above-described program expanded in the memory, this device functions by processing, storing, and outputting data on the memory and data input via the interface. Is realized.
  • Embodiment 2 Effect>
  • the ceramide-related substance can be industrialized by the method of Embodiment 1. Moreover, according to the method for producing a ceramide-related substance of the present embodiment, it is possible to divert existing equipment.
  • Example 1
  • aqueous potassium carbonate solution was used as the alkaline aqueous solution as the extraction solvent.
  • the aqueous solution was prepared by dissolving 0.5% (w / v) potassium carbonate for food additives (0.5% (w / v)) in water.
  • the hydrogen ion concentration of the aqueous solution was about pH 12.
  • 5 g of the dried beer cake was added to 50 ml of the 0.5% aqueous potassium carbonate solution and mixed.
  • heat treatment and pressure treatment were performed at 121 ° C. for 10 minutes under 2 atm.
  • the control was performed under the same conditions as described above and below except that water was used as the extraction solvent.
  • the solution after the extraction step is transferred to a filter paper on a funnel connected to a suction bottle, and placed in an aspirator.
  • the insoluble matter and the extract were separated by further suction.
  • the liquid in the arch I bottle was collected as the extract and used in the next concentration step.
  • the extract obtained in the separation step was concentrated using a rotary evaporator (EYELA, hereinafter the same) to a volume of about 1Z5 at 55 ° C. After concentration, the extract was cooled to 4 ° C to precipitate the lipid component. The precipitate was collected by centrifugation at 3000 rpm for 10 minutes at 4 ° C using a cooling centrifuge (Avanti HP-25 BECK MAN COULTER). The collected precipitate was freeze-dried by treatment at ⁇ 50 ° C. for 12 hours using a freeze-drying apparatus (EYELA). The obtained dried product was ground until it became a powder in a mortar and used as a subsequent sample.
  • EYELA rotary evaporator
  • the obtained sample was developed on thin-layer chromatography (hereinafter referred to as TLC) and then anthrone sulfate (Wako). It can be confirmed by a color experiment processed by the company.
  • Anthrone sulfate can color the purple color of hexose that constitutes the sugar chain of glycosphingolipid. If the substance developed by TLC turns purple, it means that the glycosphingolipid, that is, a ceramide-related substance, is contained in the sample.
  • FIG. 6 shows the TLC deployment results.
  • Band 1 is a sterol glycoside
  • Band 2 is a glycosylceramide.
  • Lanes A and B are derived from potassium carbonate aqueous extraction and water extraction, respectively.
  • lane A a large number of band groups 3 were detected at positions corresponding to band 2.
  • This band group is the target ceramide-related substance (group).
  • lane B derived from water extraction, neither sterol glycoside nor ceramide-related substances were detected.
  • Results As described above, according to Embodiment 1 of the present invention, it was proved that a ceramide-related substance can be extracted only with an alkaline aqueous solution without using an organic solvent. The reason why the extracted ceramide-related substances are detected as a group is that there are many types of plant-derived ceramide-related substances due to differences in the length of the constituent fatty acids.
  • Beer koji, beet fiber (sugar beet koji), Simon koji (white sesame koji), and flour were selected as plant materials.
  • the basic experimental method is the same as in Example 1. In other words, 5 g of each raw material was added to 50 ml of 0.5% aqueous potassium carbonate solution and extracted, and then the insoluble matter was separated and the extract obtained by a rotary evaporator was completely freed from moisture. All the samples obtained for each raw material were dissolved in 1 ml of ethanol (99.5%) to prepare a sample solution, and then the sample solution 101 was developed by TLC.
  • FIG. 7 shows the TLC deployment results.
  • Band 1 in lane M is 1 g of glycosylceramide derived from soybean and developed as a position marker for glycosylceramide.
  • Lane A is from Beet Fiber
  • Lane B is from Simon Crab
  • Lane C is from Beer Crab
  • Lane D is small It is a sample derived from wheat flour.
  • Band group 2 which is almost in the same position as band 1, is a ceramide-related substance.
  • most ceramide-related substances are extracted from beer lees. Thus, it was shown that beer lees contain a large amount of the desired ceramide-related substance and are preferable as a raw material.
  • Example 2 The separation process is the same as in Example 1. Here, the insoluble matter remaining on the filter paper after the separation step was recovered and again mixed with 50 ml of a new 0.5% aqueous potassium carbonate solution. As a control, the same method as in Example 1 (one extraction without recycling) was performed.
  • the basic operation is the same as the extraction process of Example 1. The only difference is that the raw material is insoluble.
  • the basic operation is the same as the separation process of Example 1.
  • the liquid in the suction bottle was collected as the second extract.
  • the extract and the second extract were mixed and completely dried at 55 ° C using a rotary evaporator, and the remaining dried product was used as a sample.
  • Figure 8 shows the TLC deployment results.
  • Lane Ml is sterol glycoside
  • Lane M2 is glycosylceramide
  • Lanes A and B are sample solutions extracted once, diluted 5 times and 10 times, respectively
  • Lanes C and D are sample solutions extracted twice. Respectively indicate 5-fold dilution and 10-fold dilution.
  • Band 1 shows sterol glycosides
  • band 2 shows soybean-derived glycosylceramides
  • band group 3 shows the target ceramide-related substances. As shown in this figure, the sample solution extracted twice recovered more ceramide-related substances than the sample extracted once.
  • Embodiment 1 It was verified whether the method of Embodiment 1 can extract a ceramide-related substance without requiring a drying step, and whether glyce oral glycolipid can be saponified at the same time.
  • Example 3 The basic operation was the same as in Example 3, and extraction was performed twice. The difference is that 50g of beer lees with a moisture content of about 60% (the helpless beer lees obtained in the normal beer production process) and 500ml of 0.5% aqueous potassium carbonate solution were used after the drying process. Heating and pressurization were carried out by heating and pressurizing for 15 minutes in a household pressure cooker instead of using an auto turve. The other parts are the same as those in the third embodiment, and a description thereof will be omitted.
  • All samples obtained after the concentration step were dissolved in 10 ml of ethanol to prepare sample solutions, of which 101 was developed with TLC. As a position marker, soybean-derived glycosylceramide 1 At g was used. [0142] ((Result))
  • FIG. 9 shows the TLC deployment results.
  • the band 1 of lane M shows glycosylceramide derived from soybean, and lane A shows the sample solution prepared in this example.
  • Band 2 shows a sterol glycoside, band 3 shows a ceramide-related substance, and band 4 shows one of glyce mouth glycolipids.
  • the target ceramide-related substance can be extracted without any problem even if the raw material containing a large amount of spinal cord is used as it is in the extraction process. That is, according to Embodiment 1, it was proved that the drying process for removing moisture from the raw material force is not necessarily required.
  • the manufacturing method of the present invention can reduce a plurality of manufacturing steps.
  • the target ceramide-related substance can be extracted as long as it has heating and pressurization functions that can be done with a domestic pressure cooker without using a specialized device such as an autoclave machine. It became clear that there was.
  • FIG. 1 is a diagram for explaining each process and its flow in Embodiment 1.
  • Fig. 6 A Extraction with aqueous potassium carbonate
  • Fig. 6 B Extraction with water
  • Figure 6 1 Soybean sterol glycoside
  • Figure 6 2 Soybean glycosinoreceramide
  • Figure 6 3 Ceramide-related substance group

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Abstract

Le problème à résoudre dans le cadre de la présente invention consiste à trouver un procédé et un appareil destinés à fabriquer une substance apparentée au céramide provenant d’un tissu biologique n’impliquant pas l’utilisation d’un solvant organique tel que de l’éthanol, ce qui est absolument nécessaire dans un procédé d'extraction classique. Le problème à résoudre consiste également à trouver un procédé et un appareil permettant de réduire le nombre d’étapes du procédé mentionné précédemment, tout en conservant une précision d'extraction identique à celle du procédé classique. La solution proposée dans la présente invention est un procédé destiné à produire une substance apparentée au céramide. Dans ce procédé, un tissu biologique est immergé dans une solution alcaline aqueuse sans effectuer aucune extraction à l’aide d’un solvant organique. A cette étape, des cellules constituant le tissu biologique sont lysées par l’alcali en vue d'extraire la substance apparentée au céramide, tout en saponifiant un glycéroglycolipide non souhaitable, également produit dans cette étape par l’alkali. Ensuite, l’extrait est séparé du matériau insoluble, avant d’être condensé, ce qui a pour effet de fabriquer la substance apparentée au céramide souhaitée.
PCT/JP2006/325075 2005-12-16 2006-12-15 Procede de fabrication d’une substance apparentee au ceramide utilisant une solution alcaline aqueuse et appareil pour la fabrication WO2007069733A1 (fr)

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WO2015185675A1 (fr) * 2014-06-04 2015-12-10 Nanoscience For Life Gmbh & Cokg Dispositif et procédés d'obtention de glycoglycérolipides et glycosphingolipides à partir de phases lipoïdes

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JPH03285653A (ja) * 1990-03-30 1991-12-16 Snow Brand Milk Prod Co Ltd 脂質代謝改善物及びその製造法
JPH10237107A (ja) * 1997-02-28 1998-09-08 Nisshin Oil Mills Ltd:The イネ科植物細胞壁由来の乳化力の優れた多糖類、これを用いる乳化剤および乳化方法
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JP2004300438A (ja) * 2003-03-20 2004-10-28 Nippon Flour Mills Co Ltd 茸類から脂質を抽出する方法、食品及び化粧料

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Publication number Priority date Publication date Assignee Title
EP2952565A1 (fr) * 2014-06-04 2015-12-09 Nanoscience for life GmbH & Co. KG Dispositif et procédé destiné à la production de glycoglycérolipides et glycosphingolipides à partir de phases lipoïdes
WO2015185675A1 (fr) * 2014-06-04 2015-12-10 Nanoscience For Life Gmbh & Cokg Dispositif et procédés d'obtention de glycoglycérolipides et glycosphingolipides à partir de phases lipoïdes
WO2015185676A1 (fr) * 2014-06-04 2015-12-10 Nanoscience For Life Gmbh & Cokg Dispositif et procédés d'obtention de glycoglycérolipides et de glycosphingolipides à partir de phases lipoïdes
US10239906B2 (en) 2014-06-04 2019-03-26 Nanoscience For Life Gmbh & Cokg Apparatus and method for obtaining glycoglycerolipids and glycosphingolipids from lipid phases

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